Microbicidal heterocycles

ABSTRACT

Compounds of the formula I Formula (I) wherein the substituents are as defined in claim  1 , are useful as active ingredients, which have microbiocidal activity, in particular fungicidal activity.

This application is a 371 of International Application No.PCT/EP2011/071037 filed Nov. 25, 2011, which claims priority to EP10192493.4 filed Nov. 25, 2010, and 11153989.6 filed Feb. 10, 2011, thecontents of which are incorporated herein by reference.

The present invention relates to heterocycles, e.g. as activeingredients, which have microbiocidal activity, in particular fungicidalactivity. The invention also relates to preparation of theseheterocycles, to heterocyclic derivatives used as intermediates in thepreparation of these heterocycles, to preparation of theseintermediates, to agrochemical compositions which comprise at least oneof the heterocycles, to preparation of these compositions and to use ofthe heterocycles or compositions in agriculture or horticulture forcontrolling or preventing infestation of plants, harvested food crops,seeds or non-living materials by phytopathogenic microorganisms,preferably fungi.

Certain heterocycles for use as fungicides are described in WO2007/014290, WO 2008/013622, WO 2008/013925, WO 2008/091580, WO2008/091594 and WO 2009/055514.

The present invention provides compounds of formula

whereinG¹ and G² are independently O or S;T is CR¹³ or N;Y¹ and Y² are independently CR¹⁴ or N;Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z, —C(═O)—N(R¹⁵)-z or —C(═S)—N(R¹⁶)-z,in each case z indicates the bond that is connected to R¹²;n is 1 or 2;p is 1 or 2, providing that when n is 2, p is 1;R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independentlyare hydrogen, halogen, cyano, C₁-C₄alkyl or C₁-C₄haloalkyl;R¹¹, R¹⁵ and R¹⁶ each independently are hydrogen, C₁-C₄alkyl,C₃-C₅cycloalkyl or C₁-C₄alkoxy;R¹² is heteroaryl, heteroarylalkyl, or is group (a)

wherein the heteroaryl and heteroarylalkyl can be optionally substitutedwith 1 to 4 R²³,each R²³ independently is halogen, hydroxyl, cyano, mercapto, nitro,C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy,C₁-C₄alkylthio, N(R²⁴)₂, phenyl or heteroaryl, wherein the phenyl andheteroaryl are optionally substituted with 1 to 3 substituentsindependently selected from halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy; andeach R²⁴ independently is hydrogen, cyano, C₁-C₄alkyl,C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkylsulfonyl orC₁-C₄haloalkylsulfonyl;or a salt or a N-oxide thereof.

Where substituents are indicated as being optionally substituted, thismeans that they may or may not carry one or more identical or differentsubstituents. Normally not more than three such optional substituentsare present at the same time.

The term “halogen” refers to fluorine, chlorine, bromine or iodine,preferably fluorine, chlorine or bromine.

Alkyl substituents may be straight-chained or branched. Alkyl on its ownor as part of another substituent is, depending upon the number ofcarbon atoms mentioned, for example, methyl, ethyl, n-propyl, n-butyl,n-pentyl, n-hexyl and the isomers thereof, for example, iso-propyl,iso-butyl, sec-butyl, tert-butyl, iso-amyl or pivaloyl.

A haloalkyl group may contain one or more identical or different halogenatoms and, for example, may stand for CH₂Cl, CHCl₂, CCl₃, CH₂F, CHF₂,CF₃, CF₃CH₂, CH₃CF₂, CF₃CF₂ or CCl₃CCl₂.

Heteroaryl stands for aromatic ring systems comprising mono-, bi- ortricyclic systems wherein at least one oxygen, nitrogen or sulfur atomis present as a ring member. Monocyclic and bicyclic aromatic ringsystems are preferred. For example, monoyclic heteoraryl may be a 5- to7-membered monocyclic aromatic ring containing one to three heteroatomsselected from oxygen, nitrogen and sulfur, more preferably selected fromnitrogen and sulfur. Bicyclic heteroaryl may be a 9- to 11-memberedbicyclic ring containing one to five heteroatoms, preferably one tothree heteroatoms, selected from oxygen, nitrogen and sulfur. Examplesare furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl,isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl,triazolyl, tetrazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl,triazinyl, tetrazinyl, indolyl, benzothiophenyl, benzofuranyl,benzimidazolyl, indazolyl, benzotriazolyl, benzothiazolyl, benzoxazolyl,imiazothiazoyl, quinolinyl, quinoxalinyl, isoquinolinyl, phthalazinyl,quinoxalinyl, quinazolinyl, cinnolinyl and naphthyridinyl. Heteroarylrings do not contain adjacent oxygen ring atoms, adjacent sulfur ringatoms or adjacent oxygen and sulfur ring atoms. A link to a heteroarylgroup can be via a carbon atom or via a nitrogen atom.

Heteroarylalkyl means a group A-B—, wherein A is a heteroaryl group asdefined above and B is an alkyl group as defined above. An example isheteroaryl-C₁-C₄alkyl, e.g. heteroaryl-methyl. Pyridyl-methyl- is aspecific example. The presence of one or more possible asymmetric carbonatoms in a compound of formula I means that the compounds may occur inoptically isomeric forms, i.e. enantiomeric or diastereomeric forms.Also atropisomers may occur as a result of restricted rotation about asingle bond. Formula I is intended to include all those possibleisomeric forms and mixtures thereof. The present invention includes allthose possible isomeric forms and mixtures thereof for a compound offormula I. Likewise, formula I is intended to include all possibletautomers. The present invention includes all possible tautomeric formsfor a compound of formula I.

In each case, the compounds of formula I according to the invention arein free form, in oxidized form as a N-oxide or in salt form, e.g. anagronomically usable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991.

Suitable salts of the compounds of formula I include those resultingafter addition of acid such as those with an inorganic mineral acid e.g.hydrochloric, hydrobromic, sulphuric, nitric or phosphoric acid, or anorganic carboxylic acid e.g. oxalic, tartaric, lactic, butyric, toluic,hexanoic or phthalic acid, or a sulfonic acid e.g. methane, benzene ortoluene sulfonic acid.

Preferably, the compound of formula I is a compound wherein:

G¹ and G² are independently O or S;

T is CR¹³ or N;

Y¹ is N;

Y² is CR¹⁴ or N;

Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z, —C(═O)—N(R¹⁵)-z or —C(═S)—N(R¹⁶)-z,in each case z indicates the bond that is connected to R¹²;

n is 1 or 2;

p is 1;

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independentlyare hydrogen, halogen, C₁-C₄alkyl or C₁-C₄haloalkyl;

R¹¹, R¹⁵ and R¹⁶ each independently are hydrogen, C₁-C₄alkyl orC₁-C₄alkoxy;

R¹² is heteroaryl which can be optionally substituted with 1 to 3 R²³,or is group (a);

each R²³ independently is halogen, hydroxyl, cyano, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, N(R²⁴)₂,phenyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl, wherein thephenyl, pyridyl, pyrazinyl, pyridazinyl and pyrimidinyl are optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄haloalkoxy; andeach R²⁴ independently is hydrogen, C₁-C₄alkyl, C₁-C₄alkylcarbonyl,C₁-C₄alkylsulfonyl or C_(r) C₄haloalkylsulfonyl.

More preferably, the compound of formula I is a compound wherein:

G¹ is O;

G² is O or S;

T is CR¹³ or N;

Y¹ is N;

Y² is CR¹⁴ or N;

Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z or —C(═O)—N(R¹⁵)-z, in each case zindicates the bond that is connected to R¹²;

n is 1 or 2;

p is 1;

R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independentlyare hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl;

R¹¹ and R¹⁵ each independently are hydrogen or C₁-C₄alkyl;

R¹² is heteroaryl which can be optionally substituted with 1 to 3 R²³,or is group (a);

each R²³ independently is halogen, hydroxyl, cyano, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, N(R²⁴)₂, phenyl or pyridyl, wherein thephenyl and pyridyl are optionally substituted with 1 to 3 substituentsindependently selected from halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy; andeach R²⁴ independently is hydrogen, C₁-C₄alkyl, C₁-C₄alkylcarbonyl orC₁-C₄alkylsulfonyl.

More preferably, the compound of formula I is a compound wherein:

G¹ is O;

G² is S;

T is CH or N;

Y¹ is N;

Y² is CH or N;

Q is —C(═O)-z, —C(═S)-z or —C(═O)—N(R¹⁵)-z, in each case z indicates thebond that is connected to R¹²;

n is 1 or 2;

p is 1;

R¹ and R² each independently are hydrogen, methyl or trifluoromethyl;

R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ each independently are hydrogen ormethyl;

R¹¹ and R¹⁵ each independently are hydrogen or methyl;

R¹² is furyl, thienyl, thiazolyl, thiadiazolyl, pyridyl, pyridazinyl,pyrazolyl, imidazothiazolyl, quinolinyl or quinoxalinyl, or is group(a), wherein the furyl, thienyl, thiazolyl, thiadiazolyl, pyridyl,pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl and quinoxalinylare optionally substituted with 1 to 3 R²³;each R²³ independently is halogen, hydroxyl, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, N(R²⁴)₂, phenyl or pyridyl, wherein thephenyl and pyridyl are optionally substituted with 1 to 3 substituentsindependently selected from halogen, cyano, methyl, halomethyl, methoxyand halomethoxy; andeach R²⁴ independently is hydrogen or C₁-C₄alkylsulfonyl.

More preferably, the compound of formula I is a compound wherein:

G¹ is O;

G² is S;

T is CH;

Y¹ is N;

Y² is CH;

Q is —C(═O)-z or —C(═S)-z in each case z indicates the bond that isconnected to R¹²;

n is 2;

p is 1;

R¹ and R² each independently are hydrogen, methyl or trifluoromethyl;

R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ each independently are hydrogen ormethyl;

R¹¹ is hydrogen or methyl; and

R¹² is thiadiazolyl or pyridyl, wherein the thiadiazolyl and pyridyl areeach optionally substituted with 1 to 3 substituents independentlyselected from halogen, hydroxyl, C₁-C₄alkyl and C₁-C₄alkoxy.

More preferably, the compound of formula I is a compound wherein:

G¹ is O;

G² is S;

T is CH;

Y¹ is N;

Y² is CH;

Q is —C(═O)-z, z indicates the bond that is connected to R¹²;

n is 2;

p is 1;

R¹ is trifluoromethyl;

R² is methyl;

R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ each independently are hydrogen;

R¹¹ is hydrogen; and

R¹² is pyridyl, optionally substituted with 1 to 3 substituentsindependently selected from halogen and hydroxyl.

The following list provides definitions, including preferreddefinitions, for substituents G¹, G², T, Y¹, Y², Q, n, p, R¹, R², R³,R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R²³ and R²⁴with reference to compounds of formula I. For any one of thesesubstituents, any of the definitions given below may be combined withany definition of any other substituent given below or elsewhere in thisdocument. The invention includes compounds of formula having allpossible combinations of substituent definitions given below. Generally,in this document any substituent definition may be combined with anyother substituent definition.

G¹ and G² are independently O or S. Preferably, G¹ is O. Preferably, G²is S.

T is CR¹³ or N. Preferably, T is CH or N, more preferably T is CH.

Y¹ and Y² are independently CR¹⁴ or N. Preferably, Y¹ is N. Preferably,Y² is CR¹⁴ or N, more preferably Y² is CH or N, even more preferably Y²is CH.

Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z, —C(═O)—N(R¹⁵)-z or —C(═S)—N(R¹⁶)-z,in each case z indicates the bond that is connected to R¹². Preferably,Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z or —C(═O)—N(R¹⁵)-z. More preferably,Q is —C(═O)-z, —C(═S)-z or —C(═O)—N(R¹⁵)-z. More preferably, Q is—C(═O)-z or —C(═S)-z. Even more preferably, Q is —C(═O)-z.

n is 1 or 2, preferably n is 2.

p is 1 or 2, providing that when n is 2, p is 1, preferably p is 1.

R¹ and R² each independently are hydrogen, halogen, cyano, C₁-C₄alkyl orC₁-C₄haloalkyl. Preferably, R¹ and R² each independently are hydrogen,halogen, C₁-C₄alkyl or C₁-C₄haloalkyl. More preferably, R¹ and R² eachindependently are hydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl. Morepreferably, R¹ and R² each independently are hydrogen, methyl orhalomethyl, more preferably hydrogen, methyl or trifluoromethyl. Evenmore preferably, R¹ is trifluoromethyl. Preferably, R² is methyl.

R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently arehydrogen, halogen, cyano, C₁-C₄alkyl or C₁-C₄haloalkyl. Preferably, R³,R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently arehydrogen, halogen, C₁-C₄alkyl or C₁-C₄haloalkyl. More preferably, R³,R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently arehydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl. Even more preferably, R³, R⁴,R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently are hydrogen ormethyl.

R¹¹, R¹⁵ and R¹⁶ each independently are hydrogen, C₁-C₄alkyl,C₃-C₅cycloalkyl or C₁-C₄alkoxy. Preferably, R¹¹, R¹⁵ and R¹⁶ eachindependently are hydrogen, C₁-C₄alkyl or C_(r) C₄alkoxy. Morepreferably, R¹¹, R¹⁵ and R¹⁶ each independently are hydrogen orC₁-C₄alkyl. More preferably, R¹¹, R¹⁵ and R¹⁶ each independently arehydrogen or methyl. Even more preferably, R¹¹, R¹⁵ and R¹⁶ eachindependently are hydrogen.

R¹² is heteroaryl (preferably heteroaryl as defined above, morepreferably furyl, thienyl, thiazolyl, thiadiazolyl, pyridyl,pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl or quinoxalinyl)which can be optionally substituted with 1 to 4 R²³ and each R²³independently is halogen, hydroxyl, cyano, mercapto, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₄haloalkoxy, C₁-C₄alkylthio, N(R²⁴)₂,phenyl or heteroaryl (preferably heteroaryl as defined above, morepreferably pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl), wherein thephenyl and heteroaryl are optionally substituted with 1 to 3substituents independently selected from halogen, cyano, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy. R¹² may be group (a)

or is group (a)

wherein q is 1, 2, or 3 and e is 1 or 2.

Preferably, R¹² is heteroaryl (preferably heteroaryl as defined above,more preferably furyl, thienyl, thiazolyl, thiadiazolyl, pyridyl,pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl or quinoxalinyl)which can be optionally substituted with 1 to 3 R²³ and each R²³independently is halogen, hydroxyl, cyano, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₄haloalkoxy, C₁-C₄alkylthio, N(R²⁴)₂,phenyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl, wherein thephenyl, pyridyl, pyrazinyl, pyridazinyl and pyrimidinyl are optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄haloalkoxy. R¹² may also be group (a) with R²³ similarly defined.

More preferably, R¹² is heteroaryl (preferably heteroaryl as definedabove, more preferably furyl, thienyl, thiazolyl, thiadiazolyl, pyridyl,pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl or quinoxalinyl)which can be optionally substituted with 1 to 3 R²³ and each R²³independently is halogen, hydroxyl, cyano, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, N(R²⁴)₂, phenyl or pyridyl, wherein thephenyl and pyridyl are optionally substituted with 1 to 3 substituentsindependently selected from halogen, cyano, C₁-C₄ alkyl, C₁-C₄haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy. R¹² may also be group (a)with R²³ similarly defined.

More preferably, R¹² is furyl, thienyl, thiazolyl, thiadiazolyl,pyridyl, pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl orquinoxalinyl, wherein the furyl, thienyl, thiazolyl, thiadiazolyl,pyridyl, pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl orquinoxalinyl are optionally substituted with 1 to 3 R²³ and each R²³independently is halogen, hydroxyl, cyano, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, N(R²⁴)₂, phenyl or pyridyl, wherein the phenyl and pyridylare optionally substituted with 1 to 3 substituents independentlyselected from halogen, cyano, methyl, halomethyl, methoxy andhalomethoxy. R¹² may also be group (a) with R²³ similarly defined.

Yet more preferably, R¹² is thiadiazolyl or pyridyl, wherein thethiadiazolyl and pyridyl are optionally substituted with 1 to 3substituents independently selected from halogen, hydroxyl, C₁-C₄alkyland C₁-C₄alkoxy.

Most preferably, R¹² is pyridyl, optionally substituted with 1 to 3substituents independently selected from halogen and hydroxyl.

Each R²⁴ independently is hydrogen, cyano, C₁-C₄alkyl,C₁-C₄alkylcarbonyl, C₁-C₄haloalkylcarbonyl, C₁-C₄alkylsulfonyl orC₁-C₄haloalkylsulfonyl. Preferably, each R²⁴ independently is hydrogen,C₁-C₄alkyl, C₁-C₄alkylcarbonyl, C₁-C₄alkylsulfonyl orC₁-C₄haloalkylsulfonyl. More preferably, each R²⁴ independently ishydrogen, C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₄alkylsulfonyl. Evenmore preferably, each R²⁴ independently is hydrogen orC₁-C₄alkylsulfonyl.

In one group of compounds R¹ is trifluoromethyl, R² is methyl, R³ and R⁴are hydrogen and G¹ is O.

In one group of compounds G² is S, Y¹ is N and Y² is CH.

In one group of compounds p is 1 and n is 2.

In one group of compounds R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ are hydrogen.

In one group of compounds Q is —C(═O)-z, wherein z indicates the bondthat is connected to R¹².

In one group of compounds R¹² is heteroaryl (preferably heteroaryl asdefined above, more preferably furyl, thienyl, thiazolyl, thiadiazolyl,pyridyl, pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl orquinoxalinyl) substituted with hydroxyl and optionally substituted withone or two further substituents. Preferably, the hydroxyl is at theortho position. Preferably, one of the further substituents is halogenand is preferably at the meta position adjacent to the hydroxyl.

In one group of compounds R¹² is group (a).

In group (a) any carbon atom in either ring may be substituted by R²³.

For the avoidance of doubt, when n is 1 and p is 1 compounds of formulaI have the formula according to formula IA:

in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², G¹, G², T,Y¹, Y² and Q have the definitions as described for formula I.

When n is 2 and p is 1, compounds of formula I have the formulaaccording to formula IB:

in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² G¹, G², T,Y¹, Y² and Q have the definitions as described for formula I.

When n is 1 and p is 2, compounds of formula I have the formulaaccording to formula IC:

in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², G¹, G², T,Y¹, Y² and Q have the definitions as described for formula I.

The invention also relates to compounds of formula IA, formula IB andformula IC as shown above.

The invention also relates to compounds of formula ID:

in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², G¹, G², T,Y¹, Y² and Q have the definitions as described for formula I. Preferreddefinitions of R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², G¹,G², T, Y¹, Y² and Q are as defined for formula I.

The invention also relates to compounds of formula IE:

in which R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², and Q havethe definitions as described for formula I. Preferred definitions of R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹² are Q are as defined forformula I.

The invention also relates to compounds of formula IF:

wherein T is CH or N, preferably CH;R¹¹ is CH₃ or H; andR¹, R² and R¹² have the definitions as described for formula I.Preferred definitions of R¹, R² and R¹² are as defined for formula I.

The invention also relates to compounds of formula IG:

wherein T is CH or N, preferably CH;R¹¹ is CH₃ or H; andR¹² has the definition as described for formula I. Preferred definitionsof R¹² are as defined for formula I.

The invention includes compounds of formula II:

in which R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², G², T, Y¹, Y², Q, n and pare as defined for formula I and R¹⁸ is hydrogen or a protecting groupsuch as alkylcarbonyl, benzyl or alkoxycarbonyl, e.g. C₁-C₄alkylcarbonyl, benzyl or C₁-C₄ alkoxycarbonyl, in particular acetyl,benzyl or tert-butoxycarbonyl. These compounds, including salts orN-oxides thereof, are useful as intermediates in the synthesis ofcompounds of formula I. Preferred definitions of R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², G², T, Y¹, Y², n and p are as defined for formula I.

The invention also includes compounds of formula III:

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹², G¹, G², Y¹, Y²,Q, n and p are as defined for formula I. These compounds, includingsalts or N-oxides thereof, are useful as intermediates in the synthesisof compounds of formula I. Preferred definitions of R¹, R², R³, R⁴, R⁵,R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹², G¹, G², Y¹, Y² n and p are as defined forformula I.

The invention also includes compounds of formula Va:

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, G¹, G², T, Y¹, Y²,n and p are as defined for formula I. These compounds, including saltsor N-oxides thereof, are useful as intermediates in the synthesis ofcompounds of formula I. Preferred definitions of R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, R¹¹, G¹, G², T, Y¹, Y², n and p are as defined forformula I.

Preferred individual compounds of formula I are:

-   4-Hydroxy-[1,2,5]thiadiazole-3-carboxylic acid    (2-{4-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-thiazol-4-yl)-amide    (Compound No. 1.g.020);-   3-Hydroxy-pyridine-2-carboxylic acid    (2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.g.023);-   4-Chloro-3-hydroxy-pyridine-2-carboxylic acid    (2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.g.024);-   3-Hydroxy-4-methoxy-pyridine-2-carboxylic acid    (2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.g.025)-   4,6-Dichloro-3-hydroxy-pyridine-2-carboxylic acid    (2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.g.026);-   5-Chloro-4-hydroxy-N-(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-nicotinamide    (Compound No. 1.g.031);-   2-Chloro-3-hydroxy-N-(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-isonicotinamide    (Compound No. 1.g.035);-   3-Hydroxy-pyridine-2-carboxylic acid    methyl-(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.h.023);-   4-Chloro-3-hydroxy-pyridine-2-carboxylic acid    methyl-(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide    (Compound No. 1.h.024);-   3-Hydroxy-pyridine-2-carboxylic acid    (2-{4-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-thiazol-4-yl)-amide    (Compound No. 1.n.023); and-   4-Chloro-3-hydroxy-pyridine-2-carboxylic acid    (2-{4-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-thiazol-4-yl)-amide    (Compound No. 1.n.024).

Compounds of the present invention can be made as shown in the followingschemes. Throughout this description, the group M, wherein R¹, R², R³,R⁴ and G¹ are as defined for formula I, stands for:

The compounds of formula IV, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹²,G², Q, T, Y¹, Y², n and p are as defined for formula I and A ishydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, can be obtained by transformation of acompound of formula V, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, G², T, Y¹,Y², n and p are as defined for formula I and A is hydrogen, a protectinggroup such as acetyl, benzyl or tert-butoxycarbonyl or a group M, with acompound of formula VI, wherein R¹² and Q are as defined for formula Iand R¹⁹ is hydroxy, halogen, preferably fluoro, chloro or bromo, oralkoxy, such as methoxy, ethoxy. This is shown in Scheme 1.

The compounds of formula VII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T,Y¹, n and p are as defined for formula I and A is hydrogen, a protectinggroup such as acetyl, benzyl or tert-butoxycarbonyl or a group M, can beobtained by transformation of a compound of formula VIII, wherein R⁵,R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T, Y¹, Y², n and p are as defined for formula Iand A is hydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, with an azide, such as diphenylphosphoryl azide and subsequent Curtius rearrangement of the resultingacyl azide with an alcohol R²⁰—OH, wherein R²⁰ is C₁-C₄alkyl oroptionally substituted aryl, and following carbamate cleavage with amineral acid, such as hydrochloric acid, sulfuric acid or an organicacid, such as trifluoroacetic acid. This is shown in Scheme 2.

The compounds of formula VIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T,Y¹, n and p are as defined for formula I and A is hydrogen, a protectinggroup such as acetyl, benzyl or tert-butoxycarbonyl or a group M, can beobtained by saponification of a compound of formula IX, wherein R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, G², T, Y¹, Y², n and p are as defined for formula I,R²⁰ is C₁-C₄alkyl or optionally substituted aryl and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, with a base such as sodium hydroxide, potassium hydroxide orlithium hydroxide. This is shown in Scheme 3.

The compounds of formula X, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G², T,Y¹, Y², n and p are as defined for formula I, R²¹ is C₁-C₄alkyl and A ishydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, can be obtained by transformation of acompound of formula XI, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G², T, Y¹,Y², n and p are as defined for formula I and A is hydrogen, a protectinggroup such as acetyl, benzyl or tert-butoxycarbonyl or a group M, withan alkyl halide R²¹-Hal, wherein R²¹ is C₁-C₄alkyl and Hal is halogen,preferably chloro or bromo. This is shown in Scheme 4.

The compounds of formula XI, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G²,T, Y¹, n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, can be obtained by transformation of a compound of formulaVIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T, Y¹, Y², n and p are asdefined for formula I and A is hydrogen, a protecting group such asacetyl, benzyl or tert-butoxycarbonyl or a group M, with an azide, suchas diphenyl phosphoryl azide and subsequent Curtius rearrangement of theresulting acyl azide with a Grignard reagent R¹²—Mg-Hal, wherein R¹² isas defined for formula I and Hal is halogen, preferably chloro, bromo oriodo, or a boronic acid R¹²—B(OH)₂, wherein R¹² is as defined forformula I and a catalyst, such as bis(1,5-cyclooctadiene)rhodium(I)hydroxide. This is shown in Scheme 5.

The compounds of formula XII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G²,T, Y¹, Y², n and p are as defined for formula I, R²¹ is C₁-C₄alkyl and Ais hydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, can be obtained by transformation of acompound of formula XIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G², T,Y¹, Y², n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, with an alkyl halide R²¹-Hal, wherein R²¹ is C₁-C₄alkyl and Halis halogen, preferably chloro or bromo. This is shown in Scheme 6.

The compounds of formula XIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G²,T, Y¹, n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, can be obtained by transformation of a compound of formulaVIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T, Y¹, Y², n and p are asdefined for formula I and A is hydrogen, a protecting group such asacetyl, benzyl or tert-butoxycarbonyl or a group M, with an azide, suchas diphenyl phosphoryl azide and subsequent Curtius rearrangement of theresulting acyl azide with an alcohol R¹²—OH, wherein R¹² is as definedfor formula I as defined for formula I. This is shown in Scheme 7.

The compounds of formula XIV, wherein R⁵, R⁶, R⁷, R⁵, R⁹, R¹⁰, R¹², G²,T, Y², n and p are as defined for formula I, R²¹ is C₁-C₄alkyl and A ishydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, can be obtained by transformation of acompound of formula XV, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G², T, Y¹,Y², n and p are as defined for formula I and A is hydrogen, a protectinggroup such as acetyl, benzyl or tert-butoxycarbonyl or a group M, withan alkyl halide R²¹-Hal, wherein R²¹ is C₁-C₄alkyl and Hal is halogen,preferably chloro or bromo. This is shown in Scheme 8.

The compounds of formula XV, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹², G²,T, Y¹, Y², n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, can be obtained by transformation of a compound of formulaVIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G², T, Y¹, Y², n and p are asdefined for formula I and A is hydrogen, a protecting group such asacetyl, benzyl or tert-butoxycarbonyl or a group M, with an azide, suchas diphenyl phosphoryl azide and subsequent Curtius rearrangement of theresulting acyl azide with an amine R¹²—NH₂, wherein R¹² is as definedfor formula I. This is shown in Scheme 9.

The compounds of formula XVI, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹², G²,Q, Y¹, Y², n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, can be obtained by reduction of a compound of formula XVII,wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹², G², Q, Y¹, Y², n and p are asdefined for formula I and A is hydrogen, a protecting group such asacetyl, benzyl or tert-butoxycarbonyl or a group M, with hydrogen and acatalyst, such as palladium on charcoal, platinum or raney-nickel. Thisis shown in Scheme 10.

The compounds of formula XVII, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, R¹¹, R¹²,G², Q, Y¹, Y², n and p are as defined for formula I and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, can be obtained by cross coupling of a compound of formulaXVIII, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, n and p are as defined for formulaI, R²² is B(OH)₂ or an ester of such a boronic acid and A is hydrogen, aprotecting group such as acetyl, benzyl or tert-butoxycarbonyl or agroup M, with a compound of formula XIX, wherein R¹¹, R¹², G², Q, Y¹,Y², n and p are as defined for formula I and Hal is halogen, preferablychloro, bromo or iodo, and a transition metal, such astetrakis(triphenylphosphine)palladium, and a ligand. This is shown inScheme 11.

Alternatively, the compounds of formula XVII, wherein R⁵, R⁶, R⁷, R⁹,R¹⁰, R¹¹, R¹², G², Q, Y¹, Y², n and p are as defined for formula I and Ais hydrogen, a protecting group such as acetyl, benzyl ortert-butoxycarbonyl or a group M, can be obtained by cross coupling of acompound of formula XX, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, G², Y¹, and Y², nand p are as defined for formula I and A is hydrogen, a protecting groupsuch as acetyl, benzyl or tert-butoxycarbonyl or a group M, with acompound of formula XXI, wherein R¹¹, R¹² and Q are as defined forformula I and a catalyst, such as Pd(OAc)₂ or copperiodide with a ligandsuch as Xantphos or dimethylethylenediamine and. This is shown in Scheme12.

The compounds of formula XX, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, G², Y¹, Y², nand p are as defined for formula I and A is hydrogen, a protecting groupsuch as acetyl, benzyl or tert-butoxycarbonyl or a group M, can beobtained by cross coupling of a compound of formula XVIII, wherein R⁵,R⁶, R⁷, R⁹, R¹⁰, n and p are as defined for formula I, R²² is B(OH)₂ oran ester of such a boronic acid and A is hydrogen, a protecting groupsuch as acetyl, benzyl or tert-butoxycarbonyl or a group M, with acompound of formula XXII, wherein G², Y¹ and Y² are as defined forformula I and Hal is halogen, preferably iodo or bromo, and a transitionmetal, such as bis-(triphenylphosphine)palladium(II) chloride. This isshown in Scheme 13.

The compounds of formula XXIII, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, G², Y¹, Y²,n and p are as defined for formula I, R²⁰ is C₁-C₄alkyl or optionallysubstituted aryl and A is hydrogen, a protecting group such as acetyl,benzyl or tert-butoxycarbonyl or a group M, can be obtained by reductionof a compound of formula XXIV, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, G², Y¹, Y²,n and p are as defined for formula I, R²⁰ is C₁-C₄alkyl or optionallysubstituted aryl and A is hydrogen, a protecting group such as acetyl,benzyl or tert-butoxycarbonyl or a group M, with hydrogen and acatalyst, such as palladium on charcoal, platinum or raney-nickel. Thisis shown in Scheme 14.

The compounds of formula XXIV, wherein R⁵, R⁶, R⁷, R⁹, R¹⁰, G², T, Y¹,Y², n and p are as defined for formula I, R²⁰ is C₁-C₄alkyl oroptionally substituted aryl and A is hydrogen, a protecting group suchas acetyl, benzyl or tert-butoxycarbonyl or a group M, can be obtainedby cross coupling of a compound of formula XVIII, wherein R⁵, R⁶, R⁷,R⁹, R¹⁰, n and p are as defined for formula I, R²² is B(OH)₂ or an esterof such a boronic acid and A is hydrogen, a protecting group such asacetyl, benzyl or tert-butoxycarbonyl or a group M, with a compound offormula XXV, wherein G², Y¹ and Y² are as defined for formula I, R²⁰ isC₁-C₄alkyl or optionally substituted aryl and Hal is halogen, preferablychloro, bromo or iodo and a transition metal, such asbis-(triphenylphosphine)palladium(II) chloride. This is shown in Scheme15.

The compounds of formula XXVI, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸,R⁹, R¹⁰, G¹, G², T, Y¹, Y², n and p are as defined for formula I and R²⁰is C₁-C₄alkyl or optionally substituted aryl can be obtained bytransformation of a compound of formula XXVII, wherein R¹, R², R³, R⁴and G¹ are as defined for formula I and R¹⁹ is hydroxyl, halogen,preferably fluoro, chloro or bromo or alkoxy, such as methoxy, ethoxy,with a compound of formula XXVIII, wherein R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, G²,T, Y¹, Y², n and p are as defined for formula I and R²⁰ is C₁-C₄alkyl oroptionally substituted aryl. This is shown in Scheme 16.

The compounds of formula I, wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², G¹, G², Q, T, Y¹, Y², n and p are as defined for formulaI can be obtained by transformation of a compound of formula XXVII,wherein R¹, R², R³, R⁴ and G¹ are as defined for formula I and R¹⁹ ishydroxyl, halogen, preferably fluoro, chloro or bromo or alkoxy, such asmethoxy, ethoxy, with a compound of formula XXIX, wherein R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁰, R¹¹, R¹², G², Q, T, Y¹, Y², n and p are as defined forformula I. This is shown in Scheme 17.

Surprisingly, it has now been found that the novel compounds of formulaI have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

The compounds of formula I can be used in the agricultural sector andrelated fields of use e.g. as active ingredients for controlling plantpests or on non-living materials for control of spoilage microorganismsor organisms potentially harmful to man. The novel compounds aredistinguished by excellent activity at low rates of application, bybeing well tolerated by plants and by being environmentally safe. Theyhave very useful curative, preventive and systemic properties and may beused for protecting numerous cultivated plants. The compounds of formulaI can be used to inhibit or destroy the pests that occur on plants orparts of plants (fruit, blossoms, leaves, stems, tubers, roots) ofdifferent crops of useful plants, while at the same time protecting alsothose parts of the plants that grow later e.g. from phytopathogenicmicroorganisms.

It is also possible to use compounds of formula I as dressing agents forthe treatment of plant propagation material, e.g., seed, such as fruits,tubers or grains, or plant cuttings (for example rice), for theprotection against fungal infections as well as against phytopathogenicfungi occurring in the soil. The propagation material can be treatedwith a composition comprising a compound of formula I before planting:seed, for example, can be dressed before being sown. The activeingredients according to the invention can also be applied to grains(coating), either by impregnating the seeds in a liquid formulation orby coating them with a solid formulation. The composition can also beapplied to the planting site when the propagation material is beingplanted, for example, to the seed furrow during sowing. The inventionrelates also to such methods of treating plant propagation material andto the plant propagation material so treated.

Furthermore the compounds according to present invention can be used forcontrolling fungi in related areas, for example in the protection oftechnical materials, including wood and wood related technical products,in food storage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g. lumber, wall boards and paint.

The compounds of formula I are, for example, effective against thephytopathogenic fungi of the following classes: Fungi imperfecti (e.g.Alternaria spp.), Basidiomycetes (e.g. Corticium spp., Ceratobasidiumspp., Waitea spp., Thanatephorus spp., Rhizoctonia spp., Hemileia spp.,Puccinia spp., Phakopsora spp., Ustilago spp., Tilletia spp.),Ascomycetes (e.g. Venturia spp., Blumeria spp., Erysiphe spp.,Podosphaera spp., Uncinula spp., Monilinia spp., Sclerotinia spp.,Colletotrichum spp., Glomerella spp., Fusarium spp., Gibberella spp.,Monographella spp., Phaeosphaeria spp., Mycosphaerella spp., Cercosporaspp., Pyrenophora spp., Rhynchosporium spp., Magnaporthe spp.,Gaeumannomyces spp., Oculimacula spp., Ramularia spp., Botryotinia spp.)and Oomycetes (e.g. Phytophthora spp., Pythium spp., Plasmopara spp.,Peronospora spp., Pseudoperonospora spp. Bremia spp). Outstandingactivity is observed against downy mildew (e.g. Plasmopara viticola) andlate blight (e.g. Phytophthora infestans). Furthermore, the novelcompounds of formula I are effective against phytopathogenic gramnegative and gram positive bacteria (e.g. Xanthomonas spp, Pseudomonasspp, Erwinia amylovora, Ralstonia spp.) and viruses (e.g. tobacco mosaicvirus).

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise the following species of plants:cereal (wheat, barley, rye, oat, rice, maize, sorghum and relatedspecies); beet (sugar beet and fodder beet); pomes, drupes and softfruit (apples, pears, plums, peaches, almonds, cherries, strawberries,raspberries and blackberries); leguminous plants (beans, lentils, peas,soybeans); oil plants (rape, mustard, poppy, olives, sunflowers,coconut, castor oil plants, cocoa beans, groundnuts); cucumber plants(pumpkins, cucumbers, melons); fibre plants (cotton, flax, hemp, jute);citrus fruit (oranges, lemons, grapefruit, mandarins); vegetables(spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes,potatoes, paprika); lauraceae (avocado, cinnamomum, camphor) or plantssuch as tobacco, nuts, coffee, eggplants, sugar cane, tea, pepper,vines, hops, bananas and natural rubber plants, as well as turf andornamentals.

The useful plants and/or target crops in accordance with the inventioninclude conventional as well as genetically enhanced or engineeredvarieties such as, for example, insect resistant (e.g. Bt. and VIPvarieties) as well as disease resistant, herbicide tolerant (e.g.glyphosate- and glufosinate-resistant maize varieties commerciallyavailable under the trade names RoundupReady® and LibertyLink®) andnematode tolerant varieties. By way of example, suitable geneticallyenhanced or engineered crop varieties include the Stoneville 5599BRcotton and Stoneville 4892BR cotton varieties.

The term “useful plants” and/or “target crops” is to be understood asincluding also useful plants that have been rendered tolerant toherbicides like bromoxynil or classes of herbicides (such as, forexample, HPPD inhibitors, ALS inhibitors, for example primisulfuron,prosulfuron and trifloxysulfuron, EPSPS(5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” and/or “target crops” is to be understood asincluding also useful plants which have been so transformed by the useof recombinant DNA techniques that they are capable of synthesising oneor more selectively acting toxins, such as are known, for example, fromtoxin-producing bacteria, especially those of the genus Bacillus.

The term “useful plants” and/or “target crops” is to be understood asincluding also useful plants which have been so transformed by the useof recombinant DNA techniques that they are capable of synthesisingantipathogenic substances having a selective action, such as, forexample, the so-called “pathogenesis-related proteins” (PRPs, see e.g.EP-A-0 392 225). Examples of such antipathogenic substances andtransgenic plants capable of synthesising such antipathogenic substancesare known, for example, from EP-A-0 392 225, WO 95/33818, and EP-A-0 353191. The methods of producing such transgenic plants are generally knownto the person skilled in the art and are described, for example, in thepublications mentioned above.

The term “locus” of a plant as used herein is intended to embrace theplace on which the plants are growing, where the plant propagationmaterials of the plants are sown or where the plant propagationmaterials of the plants will be placed into the soil. An example forsuch a locus is a field, on which crop plants are growing.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There may be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants may be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

The compounds of formula I may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solidor liquid and are substances useful in formulation technology, e.g.natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

The compounds of formula I are normally used in the form of compositionsand can be applied to the crop area or plant to be treated,simultaneously or in succession with further compounds. These furthercompounds can be e.g. fertilizers or micronutrient donors or otherpreparations, which influence the growth of plants. They can also beselective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula I may be used in the form of fungicidalcompositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula I or of at least one preferred individual compound asabove-defined, in free form or in agrochemically usable salt form, andat least one of the above-mentioned adjuvants.

The invention provides a fungicidal composition comprising at least onecompound formula I an agriculturally acceptable carrier and optionallyan adjuvant. An agricultural acceptable carrier is for example a carrierthat is suitable for agricultural use. Agricultural carriers are wellknown in the art. Preferably said fungicidal compositions may compriseat least one additional fungicidal active ingredient in addition to thecompound of formula I.

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities. Examples of suitable additional active ingredients includethe following: Azoxystrobin (131860-33-8), Dimoxystrobin (149961-52-4),Enestrobin (238410-11-2), Fluoxastrobin (193740-76-0), Kresoxim-methyl(143390-89-0), Metominostrobin (133408-50-1), Orysastrobin(248593-16-0), Picoxystrobin (117428-22-5), Pyraclostrobin(175013-18-0), trifloxystrobin (141517-21-7), Azaconazole (60207-31-0),Bromuconazole (116255-48-2), Cyproconazole (94361-06-5), Difenoconazole(119446-68-3), Diniconazole (83657-24-3), Diniconazole-M (83657-18-5),Epoxiconazole (13385-98-8), Fenbuconazole (114369-43-6), Fluquinconazole(136426-54-5), Flusilazole (85509-19-9), Flutriafol (76674-21-0),Hexaconazole (79983-71-4), Imazalil (58594-72-2), Imibenconazole(86598-92-7), Ipconazole (125225-28-7), Metconazole (125116-23-6),Myclobutanil (88671-89-0), Oxpoconazole (174212-12-5), Pefurazoate(58011-68-0), Penconazole (66246-88-6), Prochloraz (67747-09-5),Propiconazole (60207-90-1), Prothioconazole (178928-70-6), Simeconazole(149508-90-7), Tebuconazole (107534-96-3), Tetraconazole (112281-77-3),Triadimefon (43121-43-3), Triadimenol (55219-65-3), Triflumizole(99387-89-0), Triticonazole (131983-72-7), Diclobutrazol (76738-62-0),Etaconazole (60207-93-4), Fluconazole (86386-73-4), Fluconazole-cis(112839-32-4), Thiabendazole (148-79-8), Quinconazole (103970-75-8),Fenpiclonil (74738-17-3), Fludioxonil (131341-86-1), Cyprodinil(121552-61-2), Mepanipyrim (110235-47-7), Pyrimethanil (53112-28-0),Aldimorph (91315-15-0), Dodemorph (1593-77-7), Fenpropimorph(67564-91-4), Tridemorph (81412-43-3), Fenpropidin (67306-00-7),Spiroxamine (118134-30-8), Isopyrazam (881685-58-1), Sedaxane(874967-67-6), Bixafen (581809-46-3), Penthiopyrad (183675-82-3),Fluxapyroxad (907204-31-3), Boscalid (188425-85-6), Penflufen(494793-67-8), Fluopyram (658066-35-4), Mandipropamid (374726-62-2),Benthiavalicarb (413615-35-7), Dimethomorph (110488-70-5),Chlorothalonil (1897-45-6), Fluazinam (79622-59-6), Dithianon(3347-22-6), Metrafenone (220899-03-6), Tricyclazole (41814-78-2),Mefenoxam (70630-17-0), Metalaxyl (57837-19-1), Acibenzolar(126448-41-7) (Acibenzolar-5-methyl (126448-41-7)), Mancozeb(8018-01-7), Ametoctradine (865318-97-4) Cyflufenamid (180409-60-3), andKresoxim-methyl (143390-89-0), Ipconazole (125225-28-7), Amisulbrom(348635-87-0), Cyflufenamid (180409-60-3), Ethaboxam (16650-77-3),Fluopicolide (239110-15-7), Fluthianil (304900-25-2), Isotianil(224049-04-1), Proquinazid (189278-12-4), Valiphenal (283159-90-0),1-methyl-cyclopropene (3100-04-7), Trifloxystrobin (141517-21-7), Sulfur(7704-34-9), Copper ammoniumcarbonate (CAS 33113-08-5); Copper oleate(CAS 1120-44-1); Folpet (133-07-3), Quinoxyfen (124495-18-7), Captan(133-06-2), Fenhexamid (126833-17-8), Glufosinate and its salts(51276-47-2, 35597-44-5 (S-isomer)), Glyphosate (1071-83-6) and itssalts (69254-40-6 (Diammonium), 34494-04-7 (Dimethylammonium),38641-94-0 (Isopropylammonium), 40465-66-5 (Monoammonium), 70901-20-1(Potassium), 70393-85-0 (Sesquisodium), 81591-81-3 (Trimesium)),1,3-Dimethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide,1,3-Dimethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1,3-Dimethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]-amide,(5-Chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine.

Another aspect of invention is related to the use of a compound offormula I or of a preferred individual compound as above-defined, of acomposition comprising at least one compound of formula I or at leastone preferred individual compound as above-defined, or of a fungicidalmixture comprising at least one compound of formula I or at least onepreferred individual compound as above-defined, in admixture with otherfungicides, as described above, for controlling or preventinginfestation of plants, e.g. useful plants such as crop plants,propagation material thereof, e.g. seeds, harvested crops, e.g.harvested food crops, or non-living materials by phytopathogenicmicroorganisms, preferably fungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, e.g. useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.harvested food crops, or of non-living materials by phytopathogenic orspoilage microorganisms or organisms potentially harmful to man,especially fungal organisms, which comprises the application of acompound of formula I or of a preferred individual compound asabove-defined as active ingredient to the plants, to parts of the plantsor to the locus thereof, to the propagation material thereof, or to anypart of the non-living materials.

Controlling or preventing means reducing infestation by phytopathogenicor spoilage microorganisms or organisms potentially harmful to man,especially fungal organisms, to such a level that an improvement isdemonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,which comprises the application of a compound of formula I, or anagrochemical composition which contains at least one of said compounds,is foliar application. The frequency of application and the rate ofapplication will depend on the risk of infestation by the correspondingpathogen. However, the compounds of formula I can also penetrate theplant through the roots via the soil (systemic action) by drenching thelocus of the plant with a liquid formulation, or by applying thecompounds in solid form to the soil, e.g. in granular form (soilapplication). In crops of water rice such granulates can be applied tothe flooded rice field. The compounds of formula I may also be appliedto seeds (coating) by impregnating the seeds or tubers either with aliquid formulation of the fungicide or coating them with a solidformulation.

A formulation, e.g. a composition containing the compound of formula I,and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula I, may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

The agrochemical formulations and/or compositions will usually containfrom 0.1 to 99% by weight, preferably from 0.1 to 95% by weight, of thecompound of formula I, 99.9 to 1% by weight, preferably 99.8 to 5% byweight, of a solid or liquid adjuvant, and from 0 to 25% by weight,preferably from 0.1 to 25% by weight, of a surfactant.

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

Whereas it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

The following non-limiting example illustrates the above-describedinvention in more detail.

EXAMPLE 1

This Example illustrates the preparation of3-hydroxy-4-methoxy-pyridine-2-carboxylic acid(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide(Compound No. 1.g.025)

a) Preparation of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid ethyl ester

To a solution of (5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid(9.1 g, 36.1 mmol) in DMF (100 mL) is added diisopropylethylamine (45mL, 216 mmol), followed byO-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate(15.5 g, 39.7 mmol). After stirring 15 min at RT,2-piperidin-4-yl-thiazole-4-carboxylic acid ethyl ester hydrochloride(10 g, 36.1 mmol) is added to the reaction mixture. After stirringovernight at RT, solvent is evaporated and the resulting yellow oil isdissolved in ethylacetate (300 mL), washed with saturated aqueous sodiumbicarbonate solution (300 mL), 1M HCl solution (300 mL), and brine (100mL). The organic layer is dried over sodium sulfate, filtered, andevaporated under reduced pressure. The crude mixture is purified bycolumn chromatography on silica gel (dichloromethane/methanol 10:1) togive2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid ethyl ester (13.6 g, 88%). ¹H-NMR (400 MHz, CDCl₃): δ=1.40 (t, 3H),1.70-1.85 (m, 2H), 2.16-2.30 (m, 2H), 2.32 (s, 3H), 2.79-2.89 (m, 1H),3.22-3.43 (m, 1H), 4.03-4.12 (m, 1H), 4.42 (q, 3H), 4.54-4.69 (m, 1H),4.93-5.08 (2 d, 2H (diastereotopic)), 6.35 (s, 1H), 8.10 (br, 1H). MS:m/z=209 (M+1).

b) Preparation of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid

To a solution of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid ethyl ester (2.67 g, 6.2 mmol) in THF (20 mL) is added aqueoussolution of sodium hydroxide (2 M, 4.65 mL, 9.3 mmol) at RT. Afterstirring 3 h at RT, the reaction mixture is acidified with 2M aqueoussolution of HCl until pH 2-3, and the solution is extracted withethylacetate (20 mL). The aqueous layer is re-extracted withethylacetate (20 mL) and the combined organic layers are washed withbrine (10 mL), dried over sodium sulfate, filtered, and evaporated underreduced pressure to give2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid (2.33 g, 94%), which can be used in the next step without furtherpurification. ¹H-NMR (400 MHz, d₆-acetone): δ=1.69-1.82 (m, 1H),1.87-2.02 (m, 1H), 2.16-2.37 (m, 2H), 2.38 (s, 3H), 2.89-2.99 (m, 1H),3.38-3.48 (m, 2H), 4.14-4.22 (m, 1H), 4.50-4.69 (m, 1H), 5.20-5.36 (2 d,2H (diastereotopic)), 6.41, (s, 1H), 8.34 (s, 1H). MS: m/z=403 (M+1).

c) Preparation of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamicacid tert-butyl ester

To a solution of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazole-4-carboxylicacid (9.95 g, 24.74 mmol) in tert-butanol (90 mL) is added triethylamine(8.2 mL, 56.9 mmol). After stirring 30 min. at RT, diphenylphosphorylazide (10.9 mL, 49.5 mmol) is added and the reaction mixture is dividedin 6 portions and each portion was irradiated under microwave (100° C.,15 min.). After cooling to RT, all portions are combined and water (3mL) is added to the reaction mixture and stirred for 30 minutes.Acetonitrile (40 mL) is then added, followed by addition of basicAmberlyst A21. After stirring overnight at RT, the resin is filteredoff, and solvents are evaporated under reduced pressure. The residue ispurified by column chromatography on silica gel (ethylacetate/cyclohexane 7:3) to give2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamicacid tert-butyl ester (9.6 g, 82%). ¹H-NMR (400 MHz, CDCl₃): δ=1.53 (s,9H), 1.68-1.78 (m, 2H), 2.08-2.19 (m, 2H), 2.32 (s, 3H), 2.85-2.95 (m,1H), 3.10-3.20 (m, 1H), 3.23-3.34 (m, 1H), 3.97-4.04 (m, 1H), 4.50-4.58(m, 1H), 4.93-5.05 (2d, 2H, diastereotopic protons), 6.33 (s, 1H), 7.10(br, 1H), 7.30 (s, 1H). MS: m/z=474 (M+1).

d) Preparation of1-[4-(4-amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone

To a solution of2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-carbamicacid tert-butyl ester (9.6 g, 20.3 mmol) is added a solution of 4M HClin dioxane (50 mL, 203 mmol)) at RT. After stirring 2 days at RT, thesolvent is evaporated under reduced pressure. The resulting yellowishfoam is triturated with diethylether, and filtered to give1-[4-(4-Amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanonehydrochloride salt, which is suspended in aqueous saturated sodiumbicarbonate (500 mL). After stirring 30 min. at RT, the reaction mixtureis extracted with ethylacetate (500 mL). The combined organic layers arewashed with water (100 mL) and brine (100 mL), filtered, dried oversodium sulfate, and evaporated under reduced pressure to give1-[4-(4-amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone(5.63 g, 74%). ¹H-NMR (400 MHz, CDCl₃): δ=1.65-1.80 (m, 2H), 2.08-2.20(m, 2H), 2.31 (s, 3H), 2.81-2.91 (m, 1H), 3.08-3.18 (m, 1H), 3.21-3.32(m, 1H), 3.95-4.08 (m, 3H), 4.50-4.59 (m, 1H), 4.93-5.04 (2d, 2H,diastereotopic protons), 5.84 (s, 1H), 6.32 (s, 1H). MS: m/z=374 (M+1).

e) Preparation of 3-hydroxy-4-methoxy-pyridine-2-carboxylic acid(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide(Compound No. 1.g.025)

To a solution of 3-hydroxy-4-methoxy-pyridine-2-carboxylic acid acid (70mg, 0.34 mmol) in 4 ml of acetonitrile triethylamine (0.13 mL, 0.96mmol), 1-ethyl-3-dimethylaminopropyl)carbodiimide (77 mg, 0.41 mmol) and1-hydroxy-7-azabenzotriazole (53 mg, 0.38 mmol) were added at RT. Afterstirring 15 min at RT,1-[4-(4-amino-thiazol-2-yl)-piperidin-1-yl]-2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone(120 mg, 0.32 mmol) was added to the reaction mixture. After stirring 16h at RT, the reaction mixture was diluted with 20 ml of ethyl acetate.The organic layer was washed with saturated aqueous sodium bicarbonatesolution, 1 M hydrochloric acid and brine, dried over sodium sulfate andevaporated under reduced pressure. The remainder was purified by columnchromatography on silica gel (ethylacetate/cyclohexane 1:1 to 8:2) togive 3-hydroxy-4-methoxy-pyridine-2-carboxylic acid(2-{1-[2-(5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-piperidin-4-yl}-thiazol-4-yl)-amide(Compound No. 1.g.025) as a beige solid. ¹H-NMR (400 MHz, CDCl₃):δ=1.64-1.77 (m, 2H), 2.05-2.16 (m, 2H), 2.27 (s, 3H), 2.81-2.89 (m, 1H),3.12-3.28 (m, 2H), 3.92 (s, 3H), 3.94-3.99 (m, 1H), 4.44-4.51 (m, 1H),4.93 (d, 2H), 6.27 (s, 1H), 6.89 (d, 1H), 7.59 (s, 1H), 8.00 (d, 1H).MS: m/z=525 (M+1).

Table 1 below illustrates examples of individual compounds of formula Iaccording to the invention.

TABLE 1 individual compounds of formula I according to the inventionCom- pound No. R¹ G¹ Q R¹² 001 F₃C— O —C(═O)—

002 F₃C— O —C(═O)—

003 F₃C— O —C(═O)—

004 F₃C— O —C(═O)—

005 F₃C— O —C(═O)—

006 F₃C— O —C(═O)—

007 F₃C— O —C(═O)—

008 F₃C— O —C(═O)—

009 F₃C— O —C(═O)—

010 F₃C— O —C(═O)—

011 F₃C— O —C(═O)—

012 F₃C— O —C(═O)—

013 F₃C— O —C(═O)—

014 F₃C— O —C(═O)—

015 F₃C— O —C(═O)—

016 F₃C— O —C(═O)—

017 F₃C— O —C(═O)—

018 F₃C— O —C(═O)—

019 F₃C— O —C(═O)—

020 F₃C— O —C(═O)—

021 F₃C— O —C(═O)—

022 F₃C— O —C(═O)—

023 F₃C— O —C(═O)—

024 F₃C— O —C(═O)—

025 F₃C— O —C(═O)—

026 F₃C— O —C(═O)—

027 F₃C— O —C(═O)—

028 F₃C— O —C(═O)—

029 F₃C— O —C(═O)—

030 F₃C— O —C(═O)—

031 F₃C— O —C(═O)—

032 F₃C— O —C(═O)—

033 F₃C— O —C(═O)—

034 F₃C— O —C(═O)—

035 F₃C— O —C(═O)—

036 F₃C— O —C(═O)—

037 F₃C— O —C(═O)—

038 F₃C— O —C(═O)—

039 F₃C— O —C(═O)—

040 F₃C— O —C(═O)—

041 F₃C— O —C(═O)—

042 F₃C— O —C(═O)—

043 F₃C— O —C(═O)—

044 F₃C— O —C(═O)—

045 F₃C— O —C(═O)—

046 F₃C— O —C(═O)—

047 F₃C— O —C(═O)—

048 F₃C— O —C(═O)—

049 F₃C— O —C(═O)—

050 F₃C— O —C(═O)—

051 F₃C— S —C(═O)—

052 F₃C— S —C(═O)—

053 F₃C— S —C(═O)—

054 F₃C— S —C(═O)—

055 F₃C— S —C(═O)—

056 F₃C— S —C(═O)—

057 F₃C— S —C(═O)—

058 F₃C— S —C(═O)—

059 F₃C— S —C(═O)—

060 F₃C— S —C(═O)—

061 F₃C— S —C(═O)—

062 F₃C— S —C(═O)—

063 F₃C— S —C(═O)—

064 F₃C— S —C(═O)—

065 F₃C— S —C(═O)—

066 F₃C— S —C(═O)—

067 F₃C— S —C(═O)—

068 F₃C— S —C(═O)—

069 F₃C— S —C(═O)—

070 F₃C— S —C(═O)—

071 F₃C— S —C(═O)—

072 F₃C— S —C(═O)—

073 F₃C— S —C(═O)—

074 F₃C— S —C(═O)—

075 F₃C— S —C(═O)—

076 F₃C— S —C(═O)—

077 F₃C— S —C(═O)—

078 F₃C— S —C(═O)—

079 F₃C— S —C(═O)—

080 F₃C— S —C(═O)—

081 F₃C— S —C(═O)—

082 F₃C— S —C(═O)—

083 F₃C— S —C(═O)—

084 F₃C— S —C(═O)—

085 F₃C— S —C(═O)—

086 F₃C— S —C(═O)—

087 F₃C— S —C(═O)—

088 F₃C— S —C(═O)—

089 F₃C— S —C(═O)—

090 F₃C— S —C(═O)—

091 F₃C— S —C(═O)—

092 F₃C— S —C(═O)—

093 F₃C— S —C(═O)—

094 F₃C— S —C(═O)—

095 F₃C— S —C(═O)—

096 F₃C— S —C(═O)—

097 F₃C— S —C(═O)—

098 F₃C— S —C(═O)—

099 F₃C— S —C(═O)—

100 F₃C— S —C(═O)—

101 F₃C— O —C(═S)—

102 F₃C— O —C(═S)—

103 F₃C— O —C(═S)—

104 F₃C— O —C(═S)—

105 F₃C— O —C(═S)—

106 F₃C— O —C(═S)—

107 F₃C— O —C(═S)—

108 F₃C— O —C(═S)—

109 F₃C— O —C(═S)—

110 F₃C— O —C(═S)—

111 F₃C— O —C(═S)—

112 F₃C— O —C(═S)—

113 F₃C— O —C(═S)—

114 F₃C— O —C(═S)—

115 F₃C— O —C(═S)—

116 F₃C— O —C(═S)—

117 F₃C— O —C(═S)—

118 F₃C— O —C(═S)—

119 F₃C— O —C(═S)—

120 F₃C— O —C(═S)—

121 F₃C— O —C(═S)—

122 F₃C— O —C(═S)—

123 F₃C— O —C(═S)—

124 F₃C— O —C(═S)—

125 F₃C— O —C(═S)—

126 F₃C— O —C(═S)—

127 F₃C— O —C(═S)—

128 F₃C— O —C(═S)—

129 F₃C— O —C(═S)—

130 F₃C— O —C(═S)—

131 F₃C— O —C(═S)—

132 F₃C— O —C(═S)—

133 F₃C— O —C(═S)—

134 F₃C— O —C(═S)—

135 F₃C— O —C(═S)—

136 F₃C— O —C(═S)—

137 F₃C— O —C(═S)—

138 F₃C— O —C(═S)—

139 F₃C— O —C(═S)—

140 F₃C— O —C(═S)—

141 F₃C— O —C(═S)—

142 F₃C— O —C(═S)—

143 F₃C— O —C(═S)—

144 F₃C— O —C(═S)—

145 F₃C— O —C(═S)—

146 F₃C— O —C(═S)—

147 F₃C— O —C(═S)—

148 F₃C— O —C(═S)—

149 F₃C— O —C(═S)—

150 F₃C— O —C(═S)—

151 H₃C— O —C(═O)—

152 H₃C— O —C(═O)—

153 H₃C— O —C(═O)—

154 H₃C— O —C(═O)—

155 H₃C— O —C(═O)—

156 H₃C— O —C(═O)—

157 H₃C— O —C(═O)—

158 H₃C— O —C(═O)—

159 H₃C— O —C(═O)—

160 H₃C— O —C(═O)—

161 H₃C— O —C(═O)—

162 H₃C— O —C(═O)—

163 H₃C— O —C(═O)—

164 H₃C— O —C(═O)—

165 H₃C— O —C(═O)—

166 H₃C— O —C(═O)—

167 H₃C— O —C(═O)—

168 H₃C— O —C(═O)—

169 H₃C— O —C(═O)—

170 H₃C— O —C(═O)—

171 H₃C— O —C(═O)—

172 H₃C— O —C(═O)—

173 H₃C— O —C(═O)—

174 H₃C— O —C(═O)—

175 H₃C— O —C(═O)—

176 H₃C— O —C(═O)—

177 H₃C— O —C(═O)—

178 H₃C— O —C(═O)—

179 H₃C— O —C(═O)—

180 H₃C— O —C(═O)—

181 H₃C— O —C(═O)—

182 H₃C— O —C(═O)—

183 H₃C— O —C(═O)—

184 H₃C— O —C(═O)—

185 H₃C— O —C(═O)—

186 H₃C— O —C(═O)—

187 H₃C— O —C(═O)—

188 H₃C— O —C(═O)—

189 H₃C— O —C(═O)—

190 H₃C— O —C(═O)—

191 H₃C— O —C(═O)—

192 H₃C— O —C(═O)—

193 H₃C— O —C(═O)—

194 H₃C— O —C(═O)—

195 H₃C— O —C(═O)—

196 H₃C— O —C(═O)—

197 H₃C— O —C(═O)—

198 H₃C— O —C(═O)—

199 H₃C— O —C(═O)—

200 H₃C— O —C(═O)—

201 H₃C— S —C(═O)—

202 H₃C— S —C(═O)—

203 H₃C— S —C(═O)—

204 H₃C— S —C(═O)—

205 H₃C— S —C(═O)—

206 H₃C— S —C(═O)—

207 H₃C— S —C(═O)—

208 H₃C— S —C(═O)—

209 H₃C— S —C(═O)—

210 H₃C— S —C(═O)—

211 H₃C— S —C(═O)—

212 H₃C— S —C(═O)—

213 H₃C— S —C(═O)—

214 H₃C— S —C(═O)—

215 H₃C— S —C(═O)—

216 H₃C— S —C(═O)—

217 H₃C— S —C(═O)—

218 H₃C— S —C(═O)—

219 H₃C— S —C(═O)—

220 H₃C— S —C(═O)—

221 H₃C— S —C(═O)—

222 H₃C— S —C(═O)—

223 H₃C— S —C(═O)—

224 H₃C— S —C(═O)—

225 H₃C— S —C(═O)—

226 H₃C— S —C(═O)—

227 H₃C— S —C(═O)—

228 H₃C— S —C(═O)—

229 H₃C— S —C(═O)—

230 H₃C— S —C(═O)—

231 H₃C— S —C(═O)—

232 H₃C— S —C(═O)—

233 H₃C— S —C(═O)—

234 H₃C— S —C(═O)—

235 H₃C— S —C(═O)—

236 H₃C— S —C(═O)—

237 H₃C— S —C(═O)—

238 H₃C— S —C(═O)—

239 H₃C— S —C(═O)—

240 H₃C— S —C(═O)—

241 H₃C— S —C(═O)—

242 H₃C— S —C(═O)—

243 H₃C— S —C(═O)—

244 H₃C— S —C(═O)—

245 H₃C— S —C(═O)—

246 H₃C— S —C(═O)—

247 H₃C— S —C(═O)—

248 H₃C— S —C(═O)—

249 H₃C— S —C(═O)—

250 H₃C— S —C(═O)—

251 H₃C— O —C(═S)—

252 H₃C— O —C(═S)—

253 H₃C— O —C(═S)—

254 H₃C— O —C(═S)—

255 H₃C— O —C(═S)—

256 H₃C— O —C(═S)—

257 H₃C— O —C(═S)—

258 H₃C— O —C(═S)—

259 H₃C— O —C(═S)—

260 H₃C— O —C(═S)—

261 H₃C— O —C(═S)—

262 H₃C— O —C(═S)—

263 H₃C— O —C(═S)—

264 H₃C— O —C(═S)—

265 H₃C— O —C(═S)—

266 H₃C— O —C(═S)—

267 H₃C— O —C(═S)—

268 H₃C— O —C(═S)—

269 H₃C— O —C(═S)—

270 H₃C— O —C(═S)—

271 H₃C— O —C(═S)—

272 H₃C— O —C(═S)—

273 H₃C— O —C(═S)—

274 H₃C— O —C(═S)—

275 H₃C— O —C(═S)—

276 H₃C— O —C(═S)—

277 H₃C— O —C(═S)—

278 H₃C— O —C(═S)—

279 H₃C— O —C(═S)—

280 H₃C— O —C(═S)—

281 H₃C— O —C(═S)—

282 H₃C— O —C(═S)—

283 H₃C— O —C(═S)—

284 H₃C— O —C(═S)—

285 H₃C— O —C(═S)—

286 H₃C— O —C(═S)—

287 H₃C— O —C(═S)—

288 H₃C— O —C(═S)—

289 H₃C— O —C(═S)—

290 H₃C— O —C(═S)—

291 H₃C— O —C(═S)—

292 H₃C— O —C(═S)—

293 H₃C— O —C(═S)—

294 H₃C— O —C(═S)—

295 H₃C— O —C(═S)—

296 H₃C— O —C(═S)—

297 H₃C— O —C(═S)—

298 H₃C— O —C(═S)—

299 H₃C— O —C(═S)—

300 H₃C— O —C(═S)—

301 F₃C— O —C(═O)—

302 F₃C— S —C(═O)—

303 F₃C— O —C(═S)—

304 F₃C— S —C(═S)—

305 F₃C— O —C(═O)O—

306 F₃C— O —C(═O)N—

307 H₃C O —C(═O)—

308 H₃C S —C(═O)—

309 H₃C O —C(═S)—

310 H₃C S —C(═S)—

311 F₂HC— O —C(═O)—

312 F₂HC— S —C(═O)—

313 F₂HC— O —C(═S)—

314 F₂HC— S —C(═S)—

315 F₃C— O —C(═O)—

wherea) 315 compounds of formula (I.a):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.b) 315 compounds of formula (I.b):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.c) 315 compounds of formula (I.c):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.d) 315 compounds of formula (I.d):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.e) 315 compounds of formula (I.e):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.f) 315 compounds of formula (I.f):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.g) 315 compounds of formula (I.g):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.h) 315 compounds of formula (I.h):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.i) 315 compounds of formula (I.i):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.j) 315 compounds of formula (I.j):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.k) 315 compounds of formula (I.k):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.m) 315 compounds of formula (I.m):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.n) 315 compounds of formula (I.n):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.o) 315 compounds of formula (I.o):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.p) 315 compounds of formula (I.p):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.q) 315 compounds of formula (I.q):

Wherein G¹, Q, R¹ and R¹² are as defined in Table 1.r) 315 compounds of formula (I.r):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.s) 315 compounds of formula (I.s):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.t) 315 compounds of formula (I.t):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.u) 315 compounds of formula (I.u):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.v) 315 compounds of formula (I.v):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.w) 315 compounds of formula (I.w):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.x) 315 compounds of formula (I.x):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.y) 315 compounds of formula (I.y):

wherein G¹, Q, R¹ and R¹² are as defined in Table 1.

Throughout this description, LC/MS means Liquid Chromatography MassSpectroscopy and the description of the apparatus and the method is: (HP1100 HPLC from Agilent, Phenomenex Gemini C18, 3 μm particle size, 110Angström, 30×3 mm column, 1.7 mL/min., 60° C., H₂O+0.05% HCOOH(95%)/CH₃CN/MeOH 4:1+0.04% HCOOH (5%)—2 min.—CH₃CN/MeOH 4:1+0.04% HCOOH(5%)—0.8 min., ZQ Mass Spectrometer from Waters, ionization method:electrospray (ESI), Polarity: positive ions, Capillary (kV) 3.00, Cone(V) 30.00, Extractor (V) 2.00, Source Temperature (° C.) 100,Desolvation Temperature (° C.) 250, Cone Gas Flow (L/Hr) 50, DesolvationGas Flow (L/Hr) 400)).

Table 2 shows selected LC/MS data for compounds of Table 1.

TABLE 2 LC/MS data for compounds of Table 1 Compound No. LC/MS I.g.001Rt = 2.47 min; MS: m/z = 467.87 (M + 1) I.g.002 Rt = 3.28 min; MS: m/z =543.87 (M + 1) I.g.005 Rt = 2.73 min; MS: m/z = 483.85 (M + 1) I.g.006Rt = 2.96 min; MS: m/z = 560.83 (M + 1) I.g.008 Rt = 2.87 min; MS: m/z =513.86 (M + 1) I.g.009 Rt = 2.56 min; MS: m/z = 495.93 (M + 1) I.g.010Rt = 2.97 min; MS: m/z = 557.91 (M + 1) I.g.011 Rt = 3.02 min; MS: m/z =558.88 (M + 1) I.g.013 Rt = 1.80 min; MS: m/z = 467.93 (M + 1) I.g.016Rt = 3.32 min; MS: m/z = 544.87 (M + 1) I.g.017 Rt = 3.36 min; MS: m/z =574.86 (M + 1) I.g.018 Rt = 1.52 min; MS: m/z = 530.36 (M + 1) I.g.019Rt = 2.44 min; MS: m/z = 485.86 (M + 1) I.g.022 Rt = 2.99 min; MS: m/z =492.92 (M + 1) I.g.023 Rt = 1.91 min; MS: m/z = 495(M + 1) I.g.024 Rt =1.90 min; MS: m/z = 529 (M + 1) I.g.025 Rt = 1.62 min; MS: m/z =525(M + 1) I.g.027 Rt = 2.16 min; MS: m/z = 478.91 (M + 1) I.g.028 Rt =1.29 min; MS: m/z = 495.39 (M + 1) I.g.029 Rt = 2.71 min; MS: m/z =524.84 (M + 1) I.g.030 Rt = 1.59 min; MS: m/z = 495(M + 1) I.g.034 Rt =1.56 min; MS: m/z = 495(M + 1) I.g.040 Rt = 1.57 min; MS: m/z = 530(M + 1) I.g.042 Rt = 1.41 min; MS: m/z = 524.39 (M + 1) I.g.044 Rt =3.35 min; MS: m/z = 528.87 (M + 1) I.g.050 Rt = 3.03 min; MS: m/z =529.91 (M + 1) I.g.315 Rt = 1.92 min; MS: m/z = 569.75 (M + 1)

The compounds according to the present invention can be preparedaccording to the above-mentioned reaction schemes, in which, unlessotherwise stated, the definition of each variable is as defined abovefor a compound of formula (I).

BIOLOGICAL EXAMPLES Phytophthora infestans/Tomato/Leaf Disc Preventative(Tomato Late Blight)

Tomato leaf disks are placed on water agar in multiwell plates (24-wellformat) and sprayed with the formulated test compound diluted in water.The leaf disks are inoculated with a spore suspension of the fungus 1day after application. The inoculated leaf disks are incubated at 16° C.and 75% rh under a light regime of 24 h darkness followed by 12 hlight/12 h darkness in a climate cabinet and the activity of a compoundis assessed as percent disease control compared to untreated when anappropriate level of disease damage appears in untreated check leafdisks (5-7 days after application).

Compounds I.g.001, I.g.006, I.g.010, I.g.018, I.g.022, I.g.023, I.g.025,I.g.028, I.g.042, I.g.044, I.g.050 and I.g.315 at 200 ppm give at least80% disease control in this test when compared to untreated control leafdisks under the same conditions, which show extensive diseasedevelopment.

Phytophthora infestans/Potato/Preventative (Potato Late Blight)

2-week old potato plants cv. Bintje are sprayed in a spray chamber withthe formulated test compound diluted in water. The test plants areinoculated by spraying them with a sporangia suspension 2 days afterapplication. The inoculated test plants are incubated at 18° C. with 14h light/day and 100% rh in a growth chamber and the percentage leaf areacovered by disease is assessed when an appropriate level of diseaseappears on untreated check plants (5-7 days after application).

Compounds I.g.001, I.g.010, I.g.018, I.g.023, I.g.025, I.g.044 andI.g.050 at 200 ppm give at least 80% disease control in this test whencompared to untreated control leaf disks under the same conditions,which show extensive disease development.

Phytophthora infestans/Potato/Long Lasting (Potato Late Blight)

2-week old potato plants cv. Bintje are sprayed in a spray chamber withthe formulated test compound diluted in water. The test plants areinoculated by spraying them with a sporangia suspension 6 days afterapplication. The inoculated test plants are incubated at 18° C. with 14h light/day and 100% rh in a growth chamber and the percentage leaf areacovered by disease is assessed when an appropriate level of diseaseappears on untreated check plants (9-11 days after application).

Compounds I.g.001, I.g.023, I.g.025, I.g.044 and I.g.050 at 200 ppm giveat least 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Plasmopara viticola/Grape/Leaf Disc Preventative (Grape Downy Mildew)

Grape vine leaf disks are placed on water agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks are inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf disks are incubatedat 19° C. and 80% rh under a light regime of 12 h light/12 h darkness ina climate cabinet and the activity of a compound is assessed as percentdisease control compared to untreated when an appropriate level ofdisease damage appears in untreated check leaf disks (6-8 days afterapplication).

Compounds I.g.001, I.g.005, I.g.006, I.g.009, I.g.019, I.g.022, I.g.023,I.g.042 and I.g.044 at 200 ppm give at least 80% disease control in thistest when compared to untreated control leaf disks under the sameconditions, which show extensive disease development.

Plasmopara viticola/Grape/Preventative (Grape Downy Mildew)

5-week old grape seedlings cv. Gutedel are sprayed in a spray chamberwith the formulated test compound diluted in water. The test plantsplants are inoculated by spraying a sporangia suspension on their lowerleaf surface one day after application. The inoculated test plants areincubated at 22° C. and 100% rh in a greenhouse and the percentage leafarea covered by disease is assessed when an appropriate level of diseaseappears on untreated check plants (6-8 days after application).

Compounds I.g.001, I.g.005, I.g.006, I.g.009, I.g.022, I.g.023 andI.g.042 at 200 ppm give at least 80% disease control in this test whencompared to untreated control leaf disks under the same conditions,which show extensive disease development.

Plasmopara viticola/Grape/Long Lasting (Grape Downy Mildew)

5-week old grape seedlings cv. Gutedel are sprayed in a spray chamberwith the formulated test compound diluted in water. The test plants areinoculated by spraying a sporangia suspension on their lower leafsurface 6 days after application. The inoculated test plants areincubated at 22° C. and 100% rh in a greenhouse and the percentage leafarea covered by disease is assessed when an appropriate level of diseaseappears on untreated check plants (11-13 days after application).

Compounds I.g.005, I.g.006, I.g.009, I.g.022 and I.g.042 at 200 ppm giveat least 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Pythium ultimum/Liquid Culture (Seedling Damping Off)

Mycelia fragments and oospores of a newly grown liquid culture of thefungus are directly mixed into nutrient broth (PDB potato dextrosebroth). After placing a (DMSO) solution of test compound into amicrotiter plate (96-well format), the nutrient broth containing thefungal mycelia/spore mixture is added. The test plates are incubated at24° C. and the inhibition of growth is determined photometrically 2-3days after application.

Compounds I.g.018, I.g.023, I.g.025 and I.g.042 at 200 ppm give at least80% disease control in this test when compared to untreated control leafdisks under the same conditions, which show extensive diseasedevelopment.

Pythium ultimum/Cotton/Soil Drench (Seedling Damping Off)

The test is carried out in plastic containers (650 ml volume) using amixture of (50% Vermiculit+sterile 50% Cugy soil)+10% v/v water. 10seeds (cotton, cv. Sure Grow 747) are sown in 2 rows of 5 seeds percontainer (3 replicates for evaluation of the activity, 3 replicates forevaluation of phytotox). Application is carried out directly aftersowing by pouring 10 ml compound diluted in water per row over theseeds. Just afterwards the seeds are covered with a thin layer of thesame soil and the inoculation is happening. Pythium ultimum iscultivated for 14 days on carrot slices in Roux bottles. Forinoculation, the content of the Roux bottles is mixed and homogenouslydispensed over the plastic containers without further filtering (70 mlsuspension per container). Incubation conditions: 20° C., 12 h/12 hday/night period in the greenhouse. The activity of a compound isassessed as percent disease control relative to untreated check plantswhen an appropriate level of disease damage appears in untreated checkplants (13-16 days after application).

Compounds I.g.023, I.g.025, I.g.042 and I.g.315 at 200 ppm give at least80% disease control in this test when compared to untreated control leafdisks under the same conditions, which show extensive diseasedevelopment.

What is claimed is:
 1. A compound of formula I:

wherein G¹ and G² are independently O or S; T is CR¹³ or N; Y¹ and Y²are independently CR¹⁴ or N; Q is —C(═O)-z, —C(═S)-z, —C(═O)—O-z,—C(═O)—N(R¹⁵)-z or —C(═S)—N(R¹⁶)-z, in each case z indicates the bondthat is connected to R¹²; n is 1 or 2; p is 1 or 2, providing that whenn is 2, p is 1; R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴each independently are hydrogen, halogen, cyano, C₁-C₄alkyl orC₁-C₄haloalkyl; R¹¹, R¹⁵ and R¹⁶ each independently are hydrogen,C₁-C₄alkyl, C₃-C₅cycloalkyl or C₁-C₄alkoxy; R¹² is heteroaryl,heteroarylalkyl or is group (a)

wherein the heteroaryl and heteroarylalkyl can be optionally substitutedwith 1 to 4R²³; each R²³ independently is halogen, hydroxyl, cyano,mercapto, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, N(R²⁴)₂, phenyl or heteroaryl, whereinthe phenyl and heteroaryl are optionally substituted with 1 to 3substituents independently selected from halogen, cyano, C₁-C₄ alkyl,C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄ haloalkoxy; and each R²⁴independently is hydrogen, cyano, C₁-C₄alkyl, C₁-C₄alkylcarbonyl,C₁-C₄haloalkylcarbonyl, C₁-C₄alkylsulfonyl or C₁-C₄haloalkylsulfonyl; qis 1, 2 or 3; e is 1 or 2; or a salt or a N-oxide thereof.
 2. Thecompound according to claim 1, wherein G¹ and G² are independently O orS; T is CR¹³ or N; Y¹ is N; Y² is CR¹⁴ or N; Q is —C(═O)-z, —C(═S)-z,—C(═O)—O-z, —C(═O)—N(R¹⁵)-z or —C(═S)—N(R¹⁶)-z, in each case z indicatesthe bond that is connected to R¹²; n is 1 or 2; p is 1; R¹, R², R³, R⁴,R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently are hydrogen,halogen, C₁-C₄alkyl or C₁-C₄haloalkyl; R¹¹, R¹⁵ and R¹⁶ eachindependently are hydrogen, C₁-C₄alkyl or C₁-C₄alkoxy; R¹² is heteroarylwhich can be optionally substituted with 1 to 3 R²³, or group (a); eachR²³ independently is halogen, hydroxyl, cyano, nitro, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, N(R²⁴)₂,phenyl, pyridyl, pyrazinyl, pyridazinyl or pyrimidinyl, wherein thephenyl, pyridyl, pyrazinyl, pyridazinyl and pyrimidinyl are optionallysubstituted with 1 to 3 substituents independently selected fromhalogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy and C₁-C₄haloalkoxy; and each R²⁴ independently is hydrogen, C₁-C₄alkyl,C₁-C₄alkylcarbonyl, C₁-C₄alkylsulfonyl or C₁-C₄haloalkylsulfonyl; q is1, 2 or 3; e is 1 or
 2. 3. The compound according to claim 1, wherein G¹is O; G² is O or S; T is CR¹³ or N; Y¹ is N; Y² is CR¹⁴ or N; Q is—C(═O)-z, —C(═S)-z, —C(═O)—O-z or —C(═O)—N(R¹⁵)-z, in each case zindicates the bond that is connected to R¹²; n is 1 or 2; p is 1; R¹,R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹³ and R¹⁴ each independently arehydrogen, C₁-C₄alkyl or C₁-C₄haloalkyl; R¹¹ and R¹⁵ each independentlyare hydrogen or C₁-C₄alkyl; R¹² is heteroaryl which can be optionallysubstituted with 1 to 3 R²³, or group (a); each R²³ independently ishalogen, hydroxyl, cyano, nitro, C₁-C₄alkyl, C₁-C₄haloalkyl,C₁-C₄alkoxy, N(R²⁴)₂, phenyl or pyridyl, wherein the phenyl and pyridylare optionally substituted with 1 to 3 substituents independentlyselected from halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxyand C₁-C₄ haloalkoxy; and each R²⁴ independently is hydrogen,C₁-C₄alkyl, C₁-C₄alkylcarbonyl or C₁-C₄alkylsulfonyl; q is 1, 2 or 3; eis 1 or
 2. 4. The compound according to claim 1, wherein G¹ is O; G² isS; T is CH or N; Y¹ is N; Y² is CH or N; Q is —C(═O)-z, —C(═S)-z or—C(═O)—N(R¹⁵)-z, in each case z indicates the bond that is connected toR¹²; n is 1 or 2; p is 1; R¹ and R² each independently are hydrogen,methyl or trifluoromethyl; R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰ eachindependently are hydrogen or methyl; R¹¹ and R¹⁵ each independently arehydrogen or methyl; R¹² is furyl, thienyl, thiazolyl, thiadiazolyl,pyridyl, pyridazinyl, pyrazolyl, imidazothiazolyl, quinolinyl orquinoxalinyl, or group (a), wherein the furyl, thienyl, thiazolyl,thiadiazolyl, pyridyl, pyridazinyl, pyrazolyl, imidazothiazolyl,quinolinyl and quinoxalinyl are optionally substituted with 1 to 3 R²³;each R²³ independently is halogen, hydroxyl, cyano, C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, N(R²⁴)₂, phenyl and pyridyl, wherein thephenyl and pyridyl are optionally substituted with 1 to 3 substituentsindependently selected from halogen, cyano, methyl, halomethyl, methoxyand halomethoxy; and each R²⁴ independently is hydrogen orC₁-C₄alkylsulfonyl; q is 1, 2 or 3; e is 1 or
 2. 5. The compoundaccording to claim 1, wherein G¹ is O; G² is S; T is CH; Y¹ is N; Y² isCH; Q is —C(═O)-z or —C(═S)-z, in each case z indicates the bond that isconnected to R¹²; n is 2; p is 1; R¹ and R² each independently arehydrogen, methyl or trifluoromethyl; R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁰each independently are hydrogen or methyl; R¹¹ is hydrogen or methyl;and R¹² is thiadiazolyl or pyridyl, wherein the thiadiazolyl and pyridylare optionally substituted with 1 to 3 substituents independentlyselected from halogen, hydroxyl, C₁-C₄alkyl and C₁-C₁alkoxy.
 6. Thecompound according to claim 1, wherein R¹ is trifluoromethyl, R² ismethyl, R³ and R⁴ are hydrogen and G¹ is O.
 7. The compound according toclaim 1, wherein G² is S, Y¹ is N and Y² is CH.
 8. The compoundaccording to claim 1, wherein p is 1 and n is
 2. 9. The compoundaccording to claim 1, wherein R⁵, R⁶, R⁷, R⁸, R⁹ and R¹⁹ are hydrogen.10. The compound according to claim 1, wherein Q is —C(═O)-z, wherein zindicates the bond that is connected to R¹².
 11. The compound accordingto claim 1, wherein R¹² is heteroaryl substituted with hydroxyl andoptionally substituted with one or two further substituents.
 12. Thecompound according to claim 11, wherein the hydroxyl is at the orthoposition.
 13. A fungicidal composition comprising at least one compoundas defined in claim 1 and an agriculturally acceptable carrier,optionally comprising an adjuvant, and optionally comprising at leastone additional fungicidally active compound.
 14. A method of controllingor preventing an infestation of plants, propagation material thereof,harvested crops or non-living materials by phytopathogenic or spoilagemicroorganisms or organisms potentially harmful to man, which comprisesthe application of a compound as defined in claim 1, to the plant, toparts of the plants or to the locus thereof, to propagation materialthereof or to any part of the non-living materials.